Benzoyl isothiocyanate → 1-Benzoyl-3-(5-bromo-2,4-difluoro-phenyl)-thiourea

HRID 2068674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068674
[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:11]([NH:19][C:20]([NH:7][C:6]1[CH:8]=[C:2]([Br:1])[C:3]([F:10])=[CH:4][C:5]=1[F:9])=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 68284Benzoyl isothiocyanateHCID 27832955-Bromo-2,4-difluoroaniline

Produkt 1

HCID 596030931-Benzoyl-3-(5-bromo-2,4-difluoro-phenyl)-thioureaAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-2,4-difluoro aniline (1.0 g, 4.81 mmol) in acetone (25.0 mL) was added drop wise benzoyl isothiocyanate (0.71 mL, 5.29 mmol). The resulting reaction mixture was allowed to stir at room temperature for 30 min. After the completion of the reaction (TLC monitoring), the solvent was evaporated and the residue was washed with hexane and ether to get the title compound (1.70 g, quantitative yield) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 7.02-7.06 (m, 1H), 7.56 (t, J=8.0 Hz, 2H), 7.68 (t, J=7.60 Hz, 1H), 7.91 (d, J=7.60 Hz, 2H), 8.67 (t, J=7.60 Hz, 1H), 9.15 (br s, 1H) and 12.65 (br s, 1H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. customthe solvent was evaporated
  4. washthe residue was washed with hexane and ether

Quellen und Nachweise

ORD-Eintrag
ord-fcf5c8a5f46840ddb961fe040035e221
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299065B2

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